Cheap flights from Chicago Midway Airport to San José from $144
This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago Midway Airport to San José departing on 8/11. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Southwest flights from Chicago Midway Airport to San José, San José Province
Our best Southwest deals on Chicago Midway Airport to San José, San José Province flight tickets
Frontier flights from Chicago Midway Airport to San José, San José Province
Our best Frontier deals on Chicago Midway Airport to San José, San José Province flight tickets
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How to get the cheapest flight ticket from Chicago Midway Airport to San José, San José Province
Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip
What is the cheapest month to fly to San José, San José Province?
The month of August is, on average, the cheapest month to fly to San José, San José Province from Chicago Midway Airport, with most prices found around $456. If you’re not able to fly to San José, San José Province in August, then September is your next best option. Flight prices from Chicago Midway Airport to San José, San José Province during September average around $552.
What is the cheapest day to depart on your flight to San José, San José Province?
The cheapest day to depart from Chicago Midway Airport to San José, San José Province is on a Tuesday when prices can be found for as low as $581. The most expensive day to fly to San José, San José Province is Saturday, with ticket prices averaging around $823.
When to book flights from Chicago Midway Airport to San José, San José Province
Cheap Chicago Midway Airport to San José, San José Province (MDW to SJO) flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to San José, San José Province
Best Price Found | $144 |
|---|---|
Fastest flight time | 6h 45m |
Direct flights | None |
Airports in San José, San José Province | 1 airport |
How far is Chicago Midway to San José Juan Santamaria Intl by plane?
A flight from Chicago Midway to San José Juan Santamaria Intl will travel around 2210.5 mi. Typically, this will take 6h 50m by plane in normal conditions.
When did momondo last update prices for flights from Chicago Midway Airport to San José Juan Santamaria Intl Airport?
Prices for flights from Chicago Midway Airport to San José Juan Santamaria Intl Airport are updated daily.
How many operators does momondo search for flights from Chicago Midway Airport to San José Juan Santamaria Intl Airport?
As of July 2025, there are 2 operators available to choose from for flights from Chicago Midway Airport to San José Juan Santamaria Intl Airport.
How old do you have to be to fly from Chicago Midway Airport to San José Juan Santamaria Intl Airport?
The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Chicago Midway Airport to San José Juan Santamaria Intl Airport.
What documentation or ID do you need to fly to San José Juan Santamaria Intl Airport?
The travel and health documents you'll need for your trip to San José Juan Santamaria Intl Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at San José Juan Santamaria Intl Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.
What is the most popular airline from Chicago Midway Airport to San José, San José Province?
Based on momondo bookings for flights between Chicago Midway Airport and San José, San José Province, the leading airline is Southwest, making up 74% of the total bookings. Other popular airlines include Delta with 26%.
Best airlines flying from Chicago Midway Airport to San José, San José Province
Compare and see reviews for airlines that fly from Chicago Midway Airport to San José, San José Province with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $477 | Free Cancellation | Rating 8.0 4,273 reviews | |||
| PriceFrom $544 | Free Cancellation | Rating 8.0 7,973 reviews |
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Why should I use momondo to find a flight deal from Chicago to San José?
Finding the right flight to San José from Chicago is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to San José quick and easy, saving you time and money.
Can I find flights from Chicago to San José with flexible booking policies on momondo?
All flight searches from Chicago to San José on momondo can be filtered to show those which offer flexible booking policies.
How can momondo help me find flights from Chicago to San José?
momondo provides multiple filters to help you find the best flight to San José from Chicago. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.
I’m not ready to book a flight from Chicago to San José right now. Can momondo alert me if prices change?
Of course. momondo tracks the price of Chicago to San José flights. All you need is a valid email address and we will do the rest; it is that quick and easy.